Investigation of the Intermolecular Hydrogen Bonding Effects on the Intramolecular Charge Transfer Process of Coumarin 340 in Tetrahydrofuran Solvent

Li, Hui; Han, Jianhui; Zhao, Hai-Ming; Liu, Xiaochun; Sun, Chaofan; Yin, Hao; Shi, Ying

doi:10.1007/s10876-018-1371-9

Cited by 30 publications

(26 citation statements)

References 48 publications

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“…Coupling with the changed feature of bond distances, we confirm that the intramolecular hydrogen bond O-H•••N should be strengthening in the S 1 state [43][44][45][46][47][48][49][50]. Moreover, to the best of our knowledge, the simulated infrared (IR) vibrational spectra involved in hydrogen bonding moieties should be also another manner to explore excited state intramolecular hydrogen bonding dynamics [51][52][53][54][55][56][57][58][59][60][61][62][63]. Thus, we also calculated the IR vibrational spectra about the O-H stretching vibration.…”

Section: Resultssupporting

confidence: 63%

“…Therefore, we can say that our theoretical level is suitable for HBPMM system in this work. In addition, since the frontier molecular orbitals (MOs) should be a well manner to analyze the photoexcitation process [51][52][53][54][55][56][57][58][59][60][61][62][63], the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) have been shown in Figure 2. Herein, we only show these two orbitals due to the first transition (S 0 → S 1 ) mainly involved in these two orbitals.…”

Section: Resultsmentioning

confidence: 99%

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Theoretical Elaboration about Excited State Behaviors and Fluoride Anion Sensor Mechanism for 2-{[2-(2-Hydroxy-Phenyl)-1H-Benzoimidazo-5-yl]-Phenyl-Methylene} Malononitrile

Li¹

2018

JAMS

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In view of the enormous potential of fluorescence chemosensors in recent years, more and more people focus on their developments. In the present work, we theoretically investigate a novel fluorescence sensor 2-{[2-(2-Hydroxy-phenyl)-1H-benzoimidazo-5-yl]-phenyl-methylene}-malononitrile (HBPMM) [J. Lumin. 2016, 173, 165] about its excited state intramolecular proton transfer (ESIPT) and probe response mechanism. Based on density functional theory (DFT) and time-dependent density functional theory (TDDFT) methods, we focus on the S 0 -state and S 1 -state hydrogen bonds dynamical behaviors and confirm that the strengthening intramolecular hydrogen bond in the S 1 state may promote the ESIPT reaction. In view of the photoexcitation, we find that the charge redistribution around hydroxyl moiety plays important roles in providing driving force for ESIPT. And the constructed potential energy curves further verify the ESIPT process of HBPMM should be ultrafast. That is the reason why the normal HBPMM fluorescence cannot be detected in previous experiment. Further, with the addition of fluoride anions, the exothermal deprotonation process occurs spontaneously along with the intermolecular hydrogen bond O-H•••F. It reveals the uniqueness of detecting fluoride anion using HBPMM molecule. As a whole, the fluoride anion inhibits the initial ESIPT process of HBPMM, which results in different fluorescence behaviors. This work presents the clear ESIPT process and fluoride anion sensing mechanism for the novel HBPMM chemosensor.

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Section: Resultssupporting

confidence: 63%

Section: Resultsmentioning

confidence: 99%

Theoretical Elaboration about Excited State Behaviors and Fluoride Anion Sensor Mechanism for 2-{[2-(2-Hydroxy-Phenyl)-1H-Benzoimidazo-5-yl]-Phenyl-Methylene} Malononitrile

Li¹

2018

JAMS

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“…In addition, given the variations of hydrogen bond O2—H3···N4, we find the O2—H3 bond is elongated from S 0 ‐state 0.993 Å to S 1 ‐state 1.004 Å, while the H3···N4 bond distance is shortened from S 0 ‐state 1.734 Å to S 1 ‐state 1.675 Å. All the differences of bond distances between S 0 state and S 1 state indicate the intramolecular hydrogen bond O2—H3···N4 should be strengthened in the S 1 state . Particularly, the changes of bond distances for C1—O2, C5—C6, N4—C5, and C6—C1 indicate the tendency of ESIPT reaction.…”

Section: Resultsmentioning

confidence: 77%

A detailed theoretical simulation about the excited state dynamical process for the novel (benzo[d]thiazol‐2‐yl)‐5‐(9H‐carbazol‐9‐yl)phenol molecule

Zhang

Cheng

et al. 2019

J of Physical Organic Chem

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Given that molecular excited state dynamical process plays important roles in designing and developing novel applications in recent years. In this work, based on density functional theory (DFT) and time‐dependent density functional theory (TDDFT) methods, we theoretically explored the novel (benzo[d]thiazol‐2‐yl)‐5‐(9H‐carbazol‐9‐yl)phenol (HBT‐Cz) system about its excited state behaviors. Via simulating the electrostatic potential surface (EPS) of HBT‐Cz structure, we confirm the formation of intramolecular hydrogen bond O2—H3···N4 in the S0 state. Our theoretical dominating bond lengths, bond angles, and the infrared (IR) vibrational spectra involved in hydrogen bond demonstrate that O2—H3···N4 should be strengthened in the S1 state. Upon the photoexcitation, we find the charge transfer characteristics around hydrogen bonding moieties play important roles in facilitating excited state intramolecular proton transfer (ESIPT) process. Via constructing potential energy curves, we confirm the ESIPT reaction that further explains previous experimental phenomenon. Moreover, we also search the S1‐state transition state (TS) structure along with ESIPT path, based on which we simulate the intrinsic reaction coordinate (IRC) path. Combing with the atom‐centered density matrix propagation (ADMP) molecular dynamics simulation, we further confirm the ESIPT mechanism presented in this work. We sincerely hope that our theoretical work could guide novel applications based on HBT‐Cz system in future.

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“…Till now, many different sensing mechanisms, such as intramolecular charge transfer (ICT), photo‐induced electron transfer (PET), fluorescence resonance energy transfer (FRET), and excited state proton transfer (ESPT) and so forth, are relevant with intra‐ or inter‐ molecular hydrogen bond. Particularly, the excited state inter‐ and intra‐ molecular proton transfer (ESIPT) reactions have been drawing great attention due to their unique photo‐physical and photo‐chemical properties.…”

Section: Introductionmentioning

confidence: 99%

“…Even though this sensor has weak fluorescence, it was reported that the anion‐binding adduct of bip is expected to be highly fluorescent based on ESIPT channel experimentally, however, the mechanism of bip in excited state is very limitted. In effect, experimental spectroscopic techniques, such as steady‐state absorption spectroscopy, fluorescence spectroscopy and time resolved fluorescence spectroscopy, just provide the indirect information about photo‐physical and photo‐chemical properties . Up to now, the theoretical investigations about the bip are very scarce in addition to the experiments.…”

Section: Introductionmentioning

confidence: 99%

The revelation of ESIPT behavior and fluoride response mechanism for (E)‐2‐(((1H‐benzo[d]imidazol‐2‐yl)‐imino)methyl)‐5‐(dimethylamino)‐phenol

Zheng

Zhang

et al. 2019

J of Physical Organic Chem

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Given the tremendous potential of fluorescence sensors in recent years, in this work, as a kind of novel and few studied sensor containing both NH and OH binding sites, (E)-2- (((1H-benzo[d]imidazol-2-yl)-imino)methyl)-5-(dimethylamino)-phenol (bip) has been investigated on the excited state intramolecular proton transfer (ESIPT) based on time-dependent density functional theory (TDDFT) method. Our simulated absorption and fluorescence spectra based on the TDDFT method are in agreement with the experimental results.Two kinds of bip structures could found in the S 1 state, which could be attributed to the ESIPT reaction. Hydrogen bond strengthening has been testified in the S 1 state based on comparing staple bond lengths and bond angles involved in hydrogen bond between S 0 and S 1 states. The calculated infrared (IR) vibrational spectra at the O-H stretching vibrational region and theoretical hydrogen bonding energy also declare the phenomenon of hydrogen bond strengthening. The frontier molecular orbitals (MOs) analysis and Natural bond orbital (NBO) manifest the intramolecular charge transfer (ICT) characteristic for bip chromophore, which reveals the tendency of proton transfer.The potential energy curvess of the S 0 and S 1 states are constructed to explain the mechanism of the proton transfer in excited state in detail. Further, given fluorescence sensing mechanism, we present the addition of fluoride anion can spontaneously capture the hydrogen proton of hydroxyl forming intermolecular hydrogen bond O-H···F, which results in the formation of anion product with response fluoride anion.

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Investigation of the Intermolecular Hydrogen Bonding Effects on the Intramolecular Charge Transfer Process of Coumarin 340 in Tetrahydrofuran Solvent

Cited by 30 publications

References 48 publications

Theoretical Elaboration about Excited State Behaviors and Fluoride Anion Sensor Mechanism for 2-{[2-(2-Hydroxy-Phenyl)-1H-Benzoimidazo-5-yl]-Phenyl-Methylene} Malononitrile

Theoretical Elaboration about Excited State Behaviors and Fluoride Anion Sensor Mechanism for 2-{[2-(2-Hydroxy-Phenyl)-1H-Benzoimidazo-5-yl]-Phenyl-Methylene} Malononitrile

A detailed theoretical simulation about the excited state dynamical process for the novel (benzo[d]thiazol‐2‐yl)‐5‐(9H‐carbazol‐9‐yl)phenol molecule

The revelation of ESIPT behavior and fluoride response mechanism for (E)‐2‐(((1H‐benzo[d]imidazol‐2‐yl)‐imino)methyl)‐5‐(dimethylamino)‐phenol

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